CN117481984A - Supermolecule bisabolol eutectic solvent and preparation method and application thereof - Google Patents
Supermolecule bisabolol eutectic solvent and preparation method and application thereof Download PDFInfo
- Publication number
- CN117481984A CN117481984A CN202311375431.1A CN202311375431A CN117481984A CN 117481984 A CN117481984 A CN 117481984A CN 202311375431 A CN202311375431 A CN 202311375431A CN 117481984 A CN117481984 A CN 117481984A
- Authority
- CN
- China
- Prior art keywords
- bisabolol
- eutectic solvent
- supermolecule
- supramolecular
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- RGZSQWQPBWRIAQ-LSDHHAIUSA-N alpha-Bisabolol Natural products CC(C)=CCC[C@@](C)(O)[C@@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-LSDHHAIUSA-N 0.000 title claims abstract description 254
- WTVHAMTYZJGJLJ-UHFFFAOYSA-N (+)-(4S,8R)-8-epi-beta-bisabolol Natural products CC(C)=CCCC(C)C1(O)CCC(C)=CC1 WTVHAMTYZJGJLJ-UHFFFAOYSA-N 0.000 title claims abstract description 253
- 229940036350 bisabolol Drugs 0.000 title claims abstract description 253
- HHGZABIIYIWLGA-UHFFFAOYSA-N bisabolol Natural products CC1CCC(C(C)(O)CCC=C(C)C)CC1 HHGZABIIYIWLGA-UHFFFAOYSA-N 0.000 title claims abstract description 253
- RGZSQWQPBWRIAQ-CABCVRRESA-N (-)-alpha-Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 title claims abstract description 252
- 239000002904 solvent Substances 0.000 title claims abstract description 195
- 230000005496 eutectics Effects 0.000 title claims abstract description 183
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000003094 microcapsule Substances 0.000 claims abstract description 79
- 239000003446 ligand Substances 0.000 claims abstract description 50
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 17
- -1 carboxylic acid compounds Chemical group 0.000 claims abstract description 12
- 150000002989 phenols Chemical group 0.000 claims abstract description 10
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 235000013305 food Nutrition 0.000 claims abstract description 8
- 125000002015 acyclic group Chemical group 0.000 claims abstract description 6
- 230000036541 health Effects 0.000 claims abstract description 6
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical group O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 claims abstract description 4
- 150000001298 alcohols Chemical class 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 56
- 239000003995 emulsifying agent Substances 0.000 claims description 36
- 229940101578 microlipid Drugs 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 32
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000839 emulsion Substances 0.000 claims description 25
- 238000002156 mixing Methods 0.000 claims description 23
- 238000010008 shearing Methods 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000001816 cooling Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- YJCJVMMDTBEITC-UHFFFAOYSA-N 10-hydroxycapric acid Chemical compound OCCCCCCCCCC(O)=O YJCJVMMDTBEITC-UHFFFAOYSA-N 0.000 claims description 8
- UILPJVPSNHJFIK-UHFFFAOYSA-N Paeonol Chemical compound COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 claims description 8
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 8
- 238000004090 dissolution Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 6
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 6
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005639 Lauric acid Substances 0.000 claims description 5
- 239000005642 Oleic acid Substances 0.000 claims description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 5
- 235000019136 lipoic acid Nutrition 0.000 claims description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- 235000021313 oleic acid Nutrition 0.000 claims description 5
- 229960002663 thioctic acid Drugs 0.000 claims description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 4
- 229940082500 cetostearyl alcohol Drugs 0.000 claims description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 4
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 claims description 4
- YLTGFGDODHXMFB-UHFFFAOYSA-N isoacetovanillon Natural products COC1=CC=C(C(C)=O)C=C1O YLTGFGDODHXMFB-UHFFFAOYSA-N 0.000 claims description 4
- VVOAZFWZEDHOOU-UHFFFAOYSA-N magnolol Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(CC=C)=CC=C1O VVOAZFWZEDHOOU-UHFFFAOYSA-N 0.000 claims description 4
- 229940041616 menthol Drugs 0.000 claims description 4
- MLIBGOFSXXWRIY-UHFFFAOYSA-N paeonol Natural products COC1=CC=C(O)C(C(C)=O)=C1 MLIBGOFSXXWRIY-UHFFFAOYSA-N 0.000 claims description 4
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 claims description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 4
- 239000001707 (E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol Substances 0.000 claims description 3
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 3
- 239000005792 Geraniol Substances 0.000 claims description 3
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 3
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- BLUHKGOSFDHHGX-UHFFFAOYSA-N Phytol Natural products CC(C)CCCC(C)CCCC(C)CCCC(C)C=CO BLUHKGOSFDHHGX-UHFFFAOYSA-N 0.000 claims description 3
- HNZBNQYXWOLKBA-UHFFFAOYSA-N Tetrahydrofarnesol Natural products CC(C)CCCC(C)CCCC(C)=CCO HNZBNQYXWOLKBA-UHFFFAOYSA-N 0.000 claims description 3
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 3
- BOTWFXYSPFMFNR-OALUTQOASA-N all-rac-phytol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)=CCO BOTWFXYSPFMFNR-OALUTQOASA-N 0.000 claims description 3
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 3
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 3
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 3
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 3
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 3
- 229940113087 geraniol Drugs 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- 229960002446 octanoic acid Drugs 0.000 claims description 3
- BOTWFXYSPFMFNR-PYDDKJGSSA-N phytol Chemical compound CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CO BOTWFXYSPFMFNR-PYDDKJGSSA-N 0.000 claims description 3
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 claims description 2
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- MDVYIGJINBYKOM-IBSWDFHHSA-N 3-[(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxypropane-1,2-diol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OCC(O)CO MDVYIGJINBYKOM-IBSWDFHHSA-N 0.000 claims description 2
- CSHZYWUPJWVTMQ-UHFFFAOYSA-N 4-n-Butylresorcinol Chemical compound CCCCC1=CC=C(O)C=C1O CSHZYWUPJWVTMQ-UHFFFAOYSA-N 0.000 claims description 2
- CCOQPGVQAWPUPE-UHFFFAOYSA-N 4-tert-butylcyclohexan-1-ol Chemical compound CC(C)(C)C1CCC(O)CC1 CCOQPGVQAWPUPE-UHFFFAOYSA-N 0.000 claims description 2
- 244000144730 Amygdalus persica Species 0.000 claims description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 2
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 239000005770 Eugenol Substances 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 claims description 2
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 2
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- 229940116229 borneol Drugs 0.000 claims description 2
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- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 claims description 2
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- 235000010445 lecithin Nutrition 0.000 claims description 2
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- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 claims description 2
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- 229940079781 sodium cocoyl glutamate Drugs 0.000 claims description 2
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 claims description 2
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- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 claims description 2
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- IKGKWKGYFJBGQJ-UHFFFAOYSA-M sodium;2-(dodecanoylamino)acetate Chemical compound [Na+].CCCCCCCCCCCC(=O)NCC([O-])=O IKGKWKGYFJBGQJ-UHFFFAOYSA-M 0.000 claims description 2
- IPUUFZFIUKCPJN-UHFFFAOYSA-M sodium;2-(hexadecanoylamino)acetate Chemical compound [Na+].CCCCCCCCCCCCCCCC(=O)NCC([O-])=O IPUUFZFIUKCPJN-UHFFFAOYSA-M 0.000 claims description 2
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- YBDZITJALUSANZ-UHFFFAOYSA-M sodium;2-(tetradecanoylamino)acetate Chemical compound [Na+].CCCCCCCCCCCCCC(=O)NCC([O-])=O YBDZITJALUSANZ-UHFFFAOYSA-M 0.000 claims description 2
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Abstract
The invention relates to the field of supermolecule eutectic solvents, in particular to a supermolecule bisabolol eutectic solvent, and a preparation method and application thereof. The supermolecule bisabolol eutectic solvent comprises bisabolol and ligand; the ligand comprises at least one of cyclohexanol compounds, phenolic compounds, carboxylic acid compounds, acyclic unit alcohols and polyalcohols; the molar ratio of the bisabolol to the ligand is that the bisabolol: ligand = 1: (0.1-10). The targeted design of the supermolecule bisabolol eutectic solvent ensures that the supermolecule bisabolol eutectic solvent microcapsule has the excellent characteristics of promoting solubility, enhancing transdermal penetration of active substances, co-delivering active substances and the like, and can be better applied to the fields of cosmetics, health care products, foods and the like.
Description
Technical Field
The invention relates to the field of supermolecule eutectic solvents, in particular to a supermolecule bisabolol eutectic solvent, and a preparation method and application thereof.
Background
The content of the bisabolol in the chamomile essential oil can reach 17%, and the bisabolol is mainly alpha-bisabolol, has various effects of anti-inflammatory, relieving, anti-pain, whitening and the like, and has great development value and clinical application research. The natural bisabolol has better efficacy than synthetic bisabolol, and the natural bisabolol is a viscous liquid, has slight smell, is easily dissolved in organic solvents such as methanol and ethanol, is almost insoluble in glycerol and water, and is added in an amount of more than 0.2% and less than 1.0% in a cosmetic formula, and excessive addition can reduce the efficacy of the bisabolol.
Eutectic solvents refer to stable mixtures of two or more chemical species that form a liquid state at room temperature by physical interactions. It is formed mainly by non-covalent interactions of functional groups between compounds, such as intermolecular hydrogen bonds, van der Waals forces, etc. The eutectic solvent does not change its own chemical properties relative to the precursor, but changes some physical properties such as melting point, viscosity, state, vapor pressure species properties, etc. Such non-covalently formed species are generally referred to as supramolecular species, and thus the eutectic solvent is also referred to as supramolecular solvent or supramolecular eutectic solvent. The supermolecule eutectic solvent has a plurality of excellent properties, is used for replacing organic solvents in the field of organic synthesis, has low potential toxicity, high safety and proper price, has catalytic action on reaction, mild reaction conditions, good compatibility and the like. Meanwhile, the active compound has the functions of enhancing the solubility of the active compound, enhancing the efficacy of the active compound and the like, and has wider application in the fields of cosmetics, health care products, foods and the like. The eutectic solvent is used to obtain the maximum/optimal degree of application by selecting the specific functional structure monomer due to the designability of the monomer. It is therefore critical to the choice of precursor monomers for the eutectic solvent, and the choice of the appropriate monomer may result in a synergistic effect.
The technology of micro-lipid encapsulation is the most top technology in the current skin care product permeation technology, and is the collective name of liposome, fat emulsion, micelle, vesicle, nanoparticle and Pickering emulsion. They have a particle size of 0.05-0.5 μm, can encapsulate active ingredients therein, protect the stability of active ingredients, reduce the irritation of active ingredients, enhance the transdermal effect, slow release active ingredients, targeted transport active ingredients, etc., and are widely used in cosmetics, health products, foods at present.
The bisabolol generally has the effects of anti-inflammatory, relieving and whitening, and the other monomer structure is designed to obtain the bisabolol eutectic solvent, and the bisabolol eutectic solvent is applied to the fields of cosmetics and health-care foods, so that the development of the bisabolol synergistic product has great significance.
Disclosure of Invention
The invention aims to overcome the defects existing in the prior art and provide a supermolecule bisabolol eutectic solvent, and a preparation method and application thereof; the supermolecule eutectic solvent obtained by combining bisabolol with ligand (specific functional structure monomer) has the excellent characteristics of promoting solubility, enhancing transdermal penetration of active substances, co-delivering active substances and the like, and can be better applied to the fields of cosmetics, health care products, foods and the like.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
in a first aspect, the present invention provides a supermolecule bisabolol eutectic solvent, the supermolecule bisabolol eutectic solvent consisting of bisabolol and a ligand; the ligand comprises at least one of cyclohexanol compounds, phenolic compounds, carboxylic acid compounds, acyclic unit alcohols and polyalcohols; the molar ratio of the bisabolol to the ligand is that the bisabolol: ligand = 1: (0.1-10).
In the present invention, bisabolol is mixed with a ligand such as cyclohexanol-based compound, phenol-based compound, carboxylic acid-based compound, acyclic unit alcohol, polyol, etc., and a eutectic solvent is formed by non-covalent bond action of functional groups between the compounds, for example, intermolecular hydrogen bond, van der Waals force, etc. The specific ligand of the invention is selected to interact with bisabolol, and the proportion of the ligand and the bisabolol can produce synergistic effect within the scope of the invention.
Preferably, the cyclohexanol-based compound comprises at least one of 4-tert-butylcyclohexanol, menthol, borneol, menthol lactate, menthone glycerol ketal, menthoxypropanediol; the phenolic compound comprises at least one of paeonol, 4-n-butyl resorcinol, tea polyphenol, eugenol, magnolol, thymol and peach girder; the carboxylic acid compound comprises at least one of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, 10-hydroxydecanoic acid, lipoic acid, docosahexaenoic acid and eicosapentaenoic acid; the acyclic monoalcohol comprises at least one of decanol, geraniol, phytol, octyldodecanol; the polyalcohol comprises at least one of butanediol, propylene glycol, 1, 2-hexanediol, 1, 2-pentanediol, dipropylene glycol and glycerol.
The supermolecule bisabolol eutectic solvent can be designed by selecting different ligands, which also enables the supermolecule bisabolol eutectic solvent microcapsule to be designed.
In a second aspect, the present invention provides a method for preparing the above supramolecular bisabolol eutectic solvent, comprising the following steps: mixing bisabolol and ligand under the protection of air or nitrogen, stirring, heating, fully dissolving, and cooling to obtain the supermolecule bisabolol eutectic solvent.
Preferably, the method of sufficient dissolution is: adding water or alcohol for dissolving, cooling, and removing water or alcohol.
Preferably, means such as ultrasound, grinding, homogenizing shearing, high pressure treatment, etc. may be employed to aid in the adequate dissolution of the solute.
Mixing bisabolol with ligand, mixing with or without water or alcohol, and air or nitrogen protection, applying certain physical action, and removing solution to obtain uniform stable liquid at room temperature. For ligand substances with low melting points, no solution is added for dispersion; in the case of a ligand substance having a high melting point, if the ligand is a water-soluble solid, viscous liquid or oil-soluble substance, it is necessary to disperse and dissolve the ligand substance by adding water or alcohol.
Preferably, the alcohol is at least one of methanol, ethanol, propylene glycol and butylene glycol.
Preferably, the water or alcohol is removed by freeze drying, vacuum drying, spin drying, direct drying, and the like.
In a third aspect, the present invention provides a supermolecule bisabolol eutectic solvent microcapsule, the supermolecule bisabolol eutectic solvent microcapsule comprising the supermolecule bisabolol eutectic solvent, an emulsifier and a solution as described above; the solution is at least one of water and polyalcohol; the polyalcohol comprises at least one of propylene glycol, butanediol, 1, 2-pentanediol, 1, 2-hexanediol, dipropylene glycol and glycerol.
The bisabolol is modified by the supermolecule eutectic solvent to obtain the bisabolol eutectic solvent, and the microcapsule wrapping technology and the supermolecule eutectic solvent technology are used for delivering the active substance, so that the stability, the irritation and the transdermal absorption promotion effect, the slow release and the targeting effect of the active substance are improved.
Preferably, the emulsifier comprises at least one of PEG modified oil ester compounds, sorbitol polyether compounds, cetostearyl alcohol polyether-25, alkyl glycosides, sodium stearyl glutamate, sodium cocoyl glutamate, polyglycerol-10 stearate, polyglycerol-10 myristate, polyglycerol-10 laurate, sodium myristyl glutamate, sodium lauroyl glutamate, sodium stearoyl glycinate, sodium oleoyl glycinate, sodium palmitoyl glycinate, sodium myristoyl glycinate, sodium lauroyl glycinate, sodium stearate, oleic acid, sodium palmitate, sodium myristate, lauric acid and sodium/potassium salts thereof, lecithin, soybean phospholipids, hydrogenated lecithin.
Preferably, the weight parts ratio of the supermolecule bisabolol eutectic solvent, the emulsifier and the solution is that the supermolecule bisabolol eutectic solvent: emulsifying agent: solution= (0.5-20): (0.5-20): (44-99).
In the specific range of the invention, the prepared supermolecule bisabolol eutectic solvent microcapsule has the excellent characteristics of promoting solubility, enhancing transdermal penetration of active substances, slow release, targeting and the like.
In a fourth aspect, the invention provides a preparation method of the supermolecule bisabolol eutectic solvent microcapsule, comprising the following steps:
(1) Mixing the supermolecule bisabolol eutectic solvent, the emulsifying agent and the solution, and homogenizing and shearing to obtain a primary emulsion;
(2) And (3) carrying out high-pressure homogenizing shearing on the primary emulsion obtained in the step (1) to obtain the supermolecule bisabolol eutectic solvent microcapsule.
Under the high-pressure homogenization, the supermolecule bisabolol eutectic solvent, the emulsifier and the solution form uniform and stable supermolecule bisabolol eutectic solvent microcapsule.
Preferably, in the step (2), the conditions of high-pressure homogenizing shearing are that the temperature is 20-100 ℃ and the pressure is 0-2000bar. (or equivalent scaled psi value).
Preferably, the equipment used for high-pressure homogenization is a high-pressure homogenizer, a high-pressure micro-jet, a high-pressure micro-flow control and the like.
In a fifth aspect, the invention provides an application of the supermolecule bisabolol eutectic solvent microcapsule in preparing cosmetics, health-care products and foods.
The supermolecule bisabolol eutectic solvent microcapsule can be applied to the technical development and application of plant extraction, synergistic permeation promotion, carrying and delivery and the like. The supermolecule bisabolol eutectic solvent microcapsule with specific design has the excellent characteristics of improving the solubility of active substances, enhancing the percutaneous permeation promotion of the active substances, co-delivering the active substances and the like.
The beneficial effects of the invention are as follows:
(1) The supermolecule bisabolol eutectic solvent microcapsule obtained by the preparation method can obtain supermolecule bisabolol eutectic solvents with different functions through designability of monomers, so that supermolecule bisabolol eutectic solvent microcapsule with different functions can be designed.
(2) The supermolecule bisabolol eutectic solvent microcapsule disclosed by the invention has excellent dissolution promotion efficiency in dissolving insoluble substances.
(3) The supermolecule bisabolol eutectic solvent microcapsule disclosed by the invention shows the synergistic delivery with an active substance, and the active substance has the effects of enhancing the permeation and absorption.
The bisabolol is modified by the supermolecule eutectic solvent to obtain the bisabolol eutectic solvent and carry the active substance, and the supermolecule bisabolol eutectic solvent and the active substance are delivered by using a micro-lipid encapsulation technology, so that the active substance has positive significance in improving the stability, the irritation, the transdermal absorption effect and the co-delivery effect of the active substance. Meanwhile, the method is also an important influence for the development and technological development of cosmetics, foods and health care products.
Drawings
FIG. 1 is an external view showing a supermolecule bisabolol eutectic solvent according to the present invention; from left to right are examples 1, 26, 22, 15, 17, respectively.
FIG. 2 is an external view showing the supermolecule bisabolol eutectic solvent micro lipid vesicles according to the invention; from left to right are examples 1, 26, 22, 15, 17, respectively.
FIG. 3 shows the particle size results of the supermolecule bisabolol eutectic solvent micro-lipid vesicles according to test example 2 of the present invention.
FIG. 4 is a graph showing the particle size of the supramolecular bisabolol eutectic solvent microcapsule prepared in the test example 2 according to the present invention.
FIG. 5 is a transmission electron microscope image of the supermolecule bisabolol eutectic solvent microcapsule prepared in the test example 2 of the present invention.
FIG. 6 shows the transdermal penetration effect of the supramolecular bisabolol eutectic solvent microcapsule prepared in the group 2 of test example 2 according to the present invention.
Detailed Description
For a better description of the objects, technical solutions and advantages of the present invention, the present invention will be further described with reference to the following specific examples.
Examples 1 to 13:
embodiments of the supermolecule bisabolol eutectic solvent micro-lipid vesicles of the invention; the supermolecule bisabolol eutectic solvent microcapsule comprises supermolecule bisabolol eutectic solvent, an emulsifying agent and a solution.
The emulsifier is PEG-400 hydrogenated castor oil.
The solution is polyalcohol and water; the polyol is butanediol.
In the supermolecule bisabolol eutectic solvent microcapsule, the weight parts of the supermolecule bisabolol eutectic solvent, the emulsifier, the polyalcohol and the water are as follows: emulsifying agent: polyol: water = 5:5:15:75.
the supermolecule bisabolol eutectic solvent consists of bisabolol and ligand; the ligand is a phenolic compound; the types of the phenolic compounds, the bisabolol and the ligand are shown in the molar ratio of Table 1.
TABLE 1 proportion of bisabolol to phenolic Compounds
Mixing bisabolol and ligand according to the mole ratio of table 1 under the protection of air or nitrogen, stirring and dissolving in the presence or absence of solvent (water or alcohol), heating to 60 ℃, cooling after mixing the two to one phase, and removing the solvent by rotary evaporation to obtain the supermolecule bisabolol eutectic solvent.
The preparation method of the supermolecule bisabolol eutectic solvent microcapsule comprises the following steps:
(1) Mixing the supermolecule bisabolol eutectic solvent, the emulsifying agent and the solution, and homogenizing and shearing to obtain a primary emulsion;
(2) Homogenizing the primary emulsion obtained in the step (1) for 4 times under high pressure at the temperature of 60 ℃ and the pressure of 600bar to obtain the supermolecule bisabolol eutectic solvent microcapsule.
Examples 14 to 20:
embodiments of the supermolecule bisabolol eutectic solvent micro-lipid vesicles of the invention; the supermolecule bisabolol eutectic solvent microcapsule comprises supermolecule bisabolol eutectic solvent, an emulsifying agent and a solution.
The emulsifier is cetostearyl alcohol polyether-25.
The solution is a polyol: water; the polyol is butanediol.
In the supermolecule bisabolol eutectic solvent microcapsule, the weight parts of the supermolecule bisabolol eutectic solvent, the emulsifier, the polyalcohol and the water are as follows: emulsifying agent: polyol: water = 5:5:15:75.
the supermolecule bisabolol eutectic solvent consists of bisabolol and ligand; the ligand is a cyclohexanol compound; the types of cyclohexanol compounds, and the mole ratios of bisabolol and ligand are shown in Table 2.
TABLE 2 proportion of bisabolol and cyclohexanol-like Compounds
Mixing bisabolol and ligand according to the mole ratio of table 2 under the protection of air or nitrogen, stirring and dissolving in the presence or absence of solvent (water or alcohol), heating to 30-80 ℃, cooling after mixing the two to form a phase, and removing the solvent by rotary evaporation to obtain the supermolecule bisabolol eutectic solvent.
The preparation method of the supermolecule bisabolol eutectic solvent microcapsule comprises the following steps:
(1) Mixing the supermolecule bisabolol eutectic solvent, the emulsifying agent and the solution, and homogenizing and shearing to obtain a primary emulsion;
(2) Homogenizing the primary emulsion obtained in the step (1) for 4 times under high pressure at the temperature of 40 ℃ and the pressure of 500bar to obtain the supermolecule bisabolol eutectic solvent microcapsule.
Examples 21 to 32:
embodiments of the supermolecule bisabolol eutectic solvent micro-lipid vesicles of the invention; the supermolecule bisabolol eutectic solvent microcapsule comprises supermolecule bisabolol eutectic solvent, an emulsifying agent and a solution.
The supermolecule bisabolol eutectic solvent consists of bisabolol and ligand; the ligand is carboxylic acid compound; the emulsifier is polyglycerol-10 stearate.
In the supermolecule bisabolol eutectic solvent microcapsule, the weight part ratio of the supermolecule bisabolol eutectic solvent and the emulsifier is that the supermolecule bisabolol eutectic solvent: emulsifier = 5:5.
the preparation method of the supermolecule bisabolol eutectic solvent microcapsule comprises the following steps:
(1) Mixing the supermolecule bisabolol eutectic solvent, the emulsifying agent and the solution, and homogenizing and shearing to obtain a primary emulsion;
(2) Homogenizing the primary emulsion obtained in the step (1) for 4 times under high pressure at the temperature of 60 ℃ and the pressure of 600bar to obtain the supermolecule bisabolol eutectic solvent microcapsule.
The carboxylic acid type of the supermolecule bisabolol eutectic solvent ligand, the mole ratio of the bisabolol to the ligand, the type of the polyalcohol in the solution and the ratio of the polyalcohol to water are shown in table 3.
Mixing bisabolol and ligand according to the mole ratio of table 3 under the protection of air or nitrogen, stirring and heating to 70-80 ℃ in the presence or absence of solvent (water or alcohol), cooling after the two are mixed into one phase, and removing the solvent by rotary evaporation to obtain the supermolecule bisabolol eutectic solvent.
TABLE 3 composition of bisabolol eutectic solvent and solution type during preparation thereof
| Molar ratio | Solution | |
| Example 21 | Bisabolol: octanoic acid=1:1 | Propylene glycol: water = 15:75 |
| Example 22 | Bisabolol: capric acid = 1:1 | PEG-400: water = 15:75 |
| Example 23 | Bisabolol: lauric acid=1:1 | Butanediol: water = 15:75 |
| Example 24 | Bisabolol: 10-hydroxydecanoic acid = 3:1 | 1, 2-pentanediol: water = 15:75 |
| Example 25 | Bisabolol: 10-hydroxydecanoic acid = 2:1 | 1, 2-hexanediol: water = 15:75 |
| Example 26 | Bisabolol: alpha-lipoic acid=1:1 | PEG-400: water = 15:75 |
| Example 27 | Bisabolol: eicosapentaenoic acid=2:1 | Dipropylene glycol: water = 15:75 |
| Example 28 | Bisabolol: docosahexaenoic acid=2:1 | Glycerol: water = 15:75 |
| Example 29 | Bisabolol: myristic acid=1:1 | Butanediol: water =25：65 |
| Example 30 | Bisabolol: palmitic acid=1:1 | Butanediol: water=45: 45 |
| Example 31 | Bisabolol: oleic acid=1:1 | Butanediol: water=65: 25 |
| Example 32 | Bisabolol: linoleic acid=1:1 | Butanediol: water=75: 15 |
Examples 33 to 43:
embodiments of the supermolecule bisabolol eutectic solvent micro-lipid vesicles of the invention; the supermolecule bisabolol eutectic solvent microcapsule comprises supermolecule bisabolol eutectic solvent, an emulsifying agent and a solution.
The emulsifier is cetostearyl alcohol polyether-25.
The solution is polyalcohol and water; the polyol is butanediol.
In the supermolecule bisabolol eutectic solvent microcapsule, the weight parts of the supermolecule bisabolol eutectic solvent, the emulsifier, the polyalcohol and the water are as follows: emulsifying agent: polyol: water = 5:5:15:75.
the supermolecule bisabolol eutectic solvent consists of bisabolol and ligand; the types of the ligands, bisabolol and the molar ratios of the ligands are shown in table 4.
TABLE 4 composition and formulation of bisabolol eutectic solvent
| Example 33 | Bisabolol: decanol=1:1 |
| Example 34 | Bisabolol: geraniol=1:1 |
| Example 35 | Bisabolol: phytol=1:1 |
| Example 36 | Bisabolol: octyl dodecanol = 1:1 |
| Example 37 | Bisabolol: butanediol = 2:1 |
| Example 38 | Bisabolol: dipropylene glycol 1:1 |
| Example 39 | Bisabolol: 1, 2-hexanediol = 1:1 |
| Example 40 | Bisabolol: glycerol=1:1 |
| Example 41 | Bisabolol: propylene glycol=1:1 |
| Example 42 | Bisabolol: 1, 2-pentanediol = 1:1 |
| Example 43 | Bisabolol: panthenol=1:1, solvent water |
Mixing bisabolol and ligand according to the mole ratio of table 2 under the protection of air or nitrogen, stirring and dissolving in the presence or absence of solvent (water or alcohol), heating to 30-80 ℃, cooling after mixing the two to form a phase, and removing the solvent by rotary evaporation to obtain the supermolecule bisabolol eutectic solvent.
The preparation method of the supermolecule bisabolol eutectic solvent microcapsule comprises the following steps:
(1) Mixing the supermolecule bisabolol eutectic solvent, the emulsifying agent and the solution, and homogenizing and shearing to obtain a primary emulsion;
(2) Homogenizing the primary emulsion obtained in the step (1) for 4 times under high pressure at the temperature of 60 ℃ and the pressure of 600bar to obtain the supermolecule bisabolol eutectic solvent microcapsule.
Examples 44 to 64:
embodiments of the supermolecule bisabolol eutectic solvent micro-lipid vesicles of the invention; the supermolecule bisabolol eutectic solvent microcapsule comprises supermolecule bisabolol eutectic solvent, an emulsifying agent and a solution.
The solution is polyalcohol and water; the polyol is butanediol.
The weight ratio of the polyol to the water is as follows: water = 15:75.
the supermolecule bisabolol eutectic solvent consists of bisabolol and ligand; the ligand is a phenolic compound; the phenolic compound is paeonol; the molar ratio of the bisabolol to the ligand is 1:1. the weight ratios of the types of the emulsifying agents, the supermolecular bisabolol eutectic solvents and the emulsifying agents are shown in table 5.
TABLE 5 composition of supermolecule bisabolol eutectic solvent micro-lipid vesicles
Mixing bisabolol and ligand according to the mole ratio of table 2 under the protection of air or nitrogen, stirring and dissolving in the presence or absence of solvent (water or alcohol), heating to 60 ℃, cooling after mixing the two to one phase, and removing the solvent by rotary evaporation to obtain the supermolecule bisabolol eutectic solvent.
The preparation method of the supermolecule bisabolol eutectic solvent microcapsule comprises the following steps:
(1) Mixing the supermolecule bisabolol eutectic solvent, the emulsifying agent and the solution, and homogenizing and shearing to obtain a primary emulsion;
(2) Homogenizing the primary emulsion obtained in the step (1) for 4 times under high pressure to obtain the supermolecule bisabolol eutectic solvent microcapsule.
Comparative examples 1 to 8:
comparative examples of supermolecule bisabolol eutectic solvent microcapsules according to the invention; the comparative example is a bisabolol microcapsule; the composition and the mass parts of the bisabolol microcapsule are the same as those of the corresponding part of the invention, and the corresponding relation is shown in table 6.
TABLE 6 composition of bisabolol microcapsule
The preparation method of the bisabolol microcapsule comprises the following steps:
(1) Mixing bisabolol, ligand and emulsifier in proportion to obtain an oil phase; mixing the solutions to obtain a water phase; adding the obtained oil phase into the water phase, mixing, homogenizing and shearing to obtain a primary emulsion;
(2) Homogenizing the primary emulsion obtained in the step (1) at a temperature of 60 ℃ and a pressure of 600bar for 4 times under high pressure to obtain the bisabolol microcapsule.
Comparative example 9:
comparative examples of supermolecule bisabolol eutectic solvent microcapsules according to the invention; the difference between this comparative example and example 1 is bisabolol: paeonol molar ratio = 30:0.5, the remainder being the same as in example 1.
The preparation method of the supermolecule bisabolol eutectic solvent micro-lipid capsule of the comparative example is the same as that of example 1.
Comparative example 10:
comparative examples of supermolecule bisabolol eutectic solvent microcapsules according to the invention; the comparative example was different from example 1 in that the high-pressure homogenizing treatment in step (2) was not performed during the preparation, and the rest was the same as example 1.
Comparative example 11:
comparative examples of supermolecule bisabolol eutectic solvent microcapsules according to the invention; the difference between this comparative example and example 1 is: the ligand without bisabolol was the same as in example 1.
The preparation method of the supermolecule bisabolol eutectic solvent micro-lipid capsule of the comparative example is the same as that of example 1.
Test example 1: appearance observation
The supermolecule bisabolol eutectic solvent and supermolecule bisabolol eutectic solvent microcapsule prepared in examples 1, 15, 17, 22 and 26 were observed in appearance, and the results are shown in fig. 1 and 2.
The prepared supermolecule bisabolol eutectic solvents are transparent solutions, examples 1, 15 and 17 are colorless and transparent, and example 26 (alpha-lipoic acid) is yellow and transparent.
The prepared supermolecule bisabolol eutectic solvent micro-lipid capsules are emulsion, and examples 1, 15 and 17 are milky white, and example 26 (alpha-lipoic acid) is pale yellow.
Test example 2: active solubilization test
Setting an experimental group and a control group, controlling the active components, namely 10.00g of bisabolol eutectic solvent, 5.00g of PEG-400 hydrogenated castor oil and 10g of butanediol, wherein the rest components are water (100% by mass), and the mass percentages of all the experimental group and the control group are the same.
Experimental group: adding the active component into the bisabolol eutectic solvent to serve as an oil phase, heating to 70-80 ℃, and taking the rest components as a uniformly mixed water phase. Adding the oil phase into the water phase, shearing and emulsifying to obtain a supermolecule bisabolol eutectic solvent microcapsule primary emulsion; homogenizing at 70-80 deg.c and 600bar pressure for 4 times to obtain supermolecule bisabolol eutectic solvent microcapsule.
Control group: the active component, the bisabolol and the ligand are simply mixed to be used as an oil phase, heated to 70-80 ℃, and the other components are uniformly mixed to be used as a water phase; adding the oil phase into the water phase, shearing and emulsifying to obtain a bisabolol primary emulsion, and homogenizing at 70-80 ℃ under high pressure of 600bar for 4 times to obtain the bisabolol micro-lipid capsule.
And washing the prepared supermolecule bisabolol eutectic solvent microcapsule and the prepared bisabolol microcapsule with water and centrifuging for 3 times after high-speed centrifugation, drying the bottom solid, and measuring the encapsulation rate of the active ingredient by a weighing mode to judge the solubilization effect of the supermolecule bisabolol eutectic solvent microcapsule on the active ingredient.
The calculation formula of the encapsulation efficiency is shown in formula (1), and the result is shown in table 7.
TABLE 7 solubilization Effect of supermolecule bisabolol eutectic solvent micro-lipid vesicles on active ingredients
It can be seen from groups 1-8 that both the supramolecular bisabolol eutectic solvent microcapsules and the bisabolol microcapsules show a consistency in the dissolution (encapsulation) of the active, i.e. the encapsulation of the active by the supramolecular bisabolol eutectic solvent microcapsules is significantly higher than the bisabolol microcapsules.
In principle, the principle is explained that the prepared supermolecule bisabolol eutectic solvent microcapsule enhances the solubility of an active substance in an oil phase by forming the bisabolol and a ligand into the eutectic solvent, and further enhances the entrapment efficiency of the supermolecule bisabolol eutectic solvent microcapsule on the active substance.
Test example 3 transdermal penetration effect test
Setting an experimental group and a control group, and controlling the mass percentage of the active component, 10.00g of the bisabolol eutectic solvent, 5.00g of PEG-400 hydrogenated castor oil, 10g of butanediol and the balance of water, wherein the mass percentage of the components of all the experimental group and the control group are the same.
Experimental group: adding the active component into the bisabolol eutectic solvent to serve as an oil phase, heating to 70-80 ℃, and taking the rest part as a water phase. Adding the oil phase into the water phase, shearing and emulsifying to obtain the primary emulsion of the super-molecular bisabolol eutectic solvent microcapsule, homogenizing at 70-80 ℃ and 600bar under high pressure for 4 times, and shearing to obtain the super-molecular bisabolol eutectic solvent microcapsule.
Control group 1: adding the active component into the bisabolol eutectic solvent to serve as an oil phase, heating to 70-80 ℃, and taking the rest part as a water phase. Adding the oil phase into the water phase, shearing and emulsifying to obtain the supermolecule bisabolol eutectic solvent microcapsule primary emulsion.
Control group 2: the active component, the bisabolol and the other ligand are simply mixed to be used as an oil phase, and are heated to 70-80 ℃ and the rest is used as a water phase. Adding the oil phase into the water phase, shearing and emulsifying to obtain the bisabolol primary emulsion, homogenizing at 70-80 ℃ and 600bar high pressure for 4 times, and shearing to obtain the bisabolol micro-lipid capsule.
Experiments were performed according to the transdermal penetration test design of table 8.
TABLE 8 design of transdermal penetration test of active ingredient by supermolecule bisabolol eutectic solvent micro-lipid vesicles
1) Particle size testing and transmission electron microscope observation
Taking supermolecule bisabolol eutectic solvent micro-lipid capsule and bisabolol micro-lipid capsule, diluting 1000 times, measuring by using a particle size potential measuring instrument, and simultaneously, performing transmission electron microscope observation. Test example 2 of the present invention the particle size results of the supermolecule bisabolol eutectic solvent micro-lipid vesicles are shown in figure 3; the particle size diagram of the supramolecular bisabolol eutectic solvent microcapsule prepared in the group 2 of test example 2 is shown in fig. 4, and the transmission electron microscope diagram is shown in fig. 5.
2) Penetration test
The prepared experimental group and control group are subjected to transdermal delivery experiments for 1h, 2h, 4h and 8h according to a pig skin permeation model by using Franz diffusion cells.
a) The intradermal retention of the active ingredient was measured by high performance liquid chromatography to characterize the transdermal efficacy of the active.
b) For haematococcus pluvialis extract, nitrogen filling protection is carried out in the transdermal process and the extraction process.
The following is the transdermal retention of different actives under different conditions, the formula is shown in formula (2), and the intradermal retention results are shown in Table 9. The transdermal penetration effect of the group 2 supramolecular bisabolol eutectic solvent micro-capsules in test example 2 of the present invention is shown in fig. 6.
TABLE 9 results of intradermal retention of active ingredients by supermolecular bisabolol eutectic solvent microcapsules
It can be seen that the particle size of the supermolecule bisabolol eutectic solvent micro-lipid vesicles after high pressure homogenization is in submicron order, while the particle size of the supermolecule bisabolol eutectic solvent micro-lipid vesicles without high pressure homogenization is in micron order. It is known from the principle of osmosis that the smaller the particle size of a substance is, the more the permeability is increased.
As can be seen from the penetration test, the intradermal retention of the supermolecule bisabolol eutectic solvent micro-lipid capsules at different time points (1 h, 2h, 4h and 4 h) is higher than that of the supermolecule bisabolol eutectic solvent micro-lipid capsule primary emulsion and the bisabolol micro-lipid capsules. The experimental group compared with the control group-1 shows that the high pressure homogenization reduces the particle size of the particles, thereby endowing the particles with better penetration. The experimental group versus the control group-2 demonstrates that the presence of the eutectic solvent also enhances the penetration of the active, allowing more transdermal absorption of the active.
Therefore, the supermolecule bisabolol eutectic solvent microcapsule combines the supermolecule eutectic solvent and the high-pressure homogenization technology, and can endow the active substance with more excellent osmotic absorption effect.
Test example 4 cell efficacy test of supermolecule bisabolol eutectic solvent micro-lipid vesicles
Cell efficacy experiments were performed according to the "experimental group" and the "control group" in test example 3. Efficacy experiments were performed according to table 10.
Table 10 Experimental design of the efficacy direction of the supermolecule bisabolol eutectic solvent micro-lipid vesicles against cells
The specific process is as follows:
anti-wrinkle cell assay: human skin fibroblast cell suspension was inoculated into 24-well plates and placed in an incubator for culture. A blank control group, a negative control group, a positive control group and a sample group are arranged. UVA (4.8J/cm) 2 ) As a stimulus, ELISA reagents were used to detect MMP-1 content in human skin fibroblasts.
Antioxidant cell experiment: skin of human bodyThe fiber cell suspension is inoculated to a 24-well plate and placed in an incubator for culture. A blank control group, a negative control group, a positive control group and a sample group are arranged. UVA (4.8J/cm) 2 ) As a stimulus, ELISA reagents were used to detect ROS content in human skin fibroblasts.
Cell tyrosinase assay: b16 mice melanoma cell suspensions were inoculated into 96-well plates and placed in an incubator for culture. A blank control group, a negative control group, a positive control group and a sample group are arranged. alpha-MSH was selected as a stimulus, and absorbance at 490nm was measured for each well to determine tyrosinase inhibition results.
Anti-inflammatory cell assay: human keratinocyte suspension was inoculated into 24-well plates and cultured in an incubator. Setting a model group, a negative control, a positive control and a sample group. LPS was selected as a stimulus and the IL-6 content of keratinocytes was detected using ELISA reagents.
The test results are shown in Table 11.
TABLE 11 results of efficacy of supermolecule bisabolol eutectic solvent micro-lipid vesicle cells
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It can be seen that the relative content of the supermolecule bisabolol eutectic solvent micro-lipid capsule in various effects is significantly lower than that of the supermolecule bisabolol eutectic solvent micro-lipid capsule primary emulsion and the bisabolol micro-lipid capsule micro-emulsion. The supermolecule bisabolol eutectic solvent microcapsule has synergistic effect on the efficacy of active substances.
1) The supermolecule bisabolol eutectic solvent microcapsule prepared by the preparation method can obtain supermolecule bisabolol eutectic solvents with different functions through designability of monomers, so that supermolecule bisabolol eutectic solvent microcapsule with different functions can be designed.
2) The supermolecule bisabolol eutectic solvent microcapsule provided by the invention has excellent dissolution promoting efficiency in promoting dissolution of active ingredients.
3) The supermolecule bisabolol eutectic solvent microcapsule disclosed by the invention shows synergistic delivery with an active substance, and the active substance has synergistic permeation absorption promotion effect.
The supermolecule bisabolol eutectic solvent microcapsule can be applied to the technical development and application of plant extraction, synergistic permeation promotion, carrying and delivery and the like. The supermolecule bisabolol eutectic solvent microcapsule with specific design has the excellent characteristics of improving the solubility, enhancing the percutaneous permeation promotion of active substances, co-delivering the active substances and the like.
Finally, it should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the scope of the present invention, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted equally without departing from the spirit and scope of the technical solution of the present invention.
Claims (10)
1. A supramolecular bisabolol eutectic solvent, wherein the supramolecular bisabolol eutectic solvent comprises bisabolol and a ligand; the ligand comprises at least one of cyclohexanol compounds, phenolic compounds, carboxylic acid compounds, acyclic unit alcohols and polyalcohols; the molar ratio of the bisabolol to the ligand is that the bisabolol: ligand = 1: (0.1-10).
2. The supramolecular bisabolol eutectic solvent of claim 1, wherein the cyclohexanol-based compound comprises at least one of 4-t-butylcyclohexanol, menthol, borneol, menthol lactate, menthone glycerol ketal, menthoxypropanediol; the phenolic compound comprises at least one of paeonol, 4-n-butyl resorcinol, tea polyphenol, eugenol, magnolol, thymol and peach girder; the carboxylic acid compound comprises at least one of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, oleic acid, linoleic acid, 10-hydroxydecanoic acid, lipoic acid, docosahexaenoic acid and eicosapentaenoic acid; the acyclic monoalcohol comprises at least one of decanol, geraniol, phytol, octyldodecanol; the polyalcohol comprises at least one of butanediol, propylene glycol, 1, 2-hexanediol, 1, 2-pentanediol, dipropylene glycol and glycerol.
3. A method for preparing the supramolecular bisabolol eutectic solvent according to claim 1 or 2, comprising the steps of: mixing bisabolol and ligand under the protection of air or nitrogen, stirring, heating, fully dissolving, and cooling to obtain the supermolecule bisabolol eutectic solvent.
4. A method of preparing the supramolecular bisabolol eutectic solvent according to claim 3, wherein the method of sufficient dissolution is: adding water or alcohol for dissolving, cooling, and removing water or alcohol.
5. A supramolecular bisabolol eutectic solvent microcapsule, comprising the supramolecular bisabolol eutectic solvent, emulsifier, and solution of any one of claims 1-2; the solution is at least one of water and polyalcohol; the polyalcohol comprises at least one of propylene glycol, butanediol, 1, 2-pentanediol, 1, 2-hexanediol, dipropylene glycol and glycerol.
6. The supramolecular bisabolol eutectic solvent microcapsule of claim 5, wherein the emulsifier comprises at least one of PEG-modified oil ester compounds, sorbitol polyether compounds, cetostearyl alcohol polyether-25, alkyl glycosides, sodium stearyl glutamate, sodium cocoyl glutamate, polyglyceryl-10 stearate, polyglyceryl-10 myristate, polyglyceryl-10 laurate, sodium myristoyl glutamate, sodium lauroyl glutamate, sodium stearoyl glycinate, sodium oleoyl glycinate, sodium palmitoyl glycinate, sodium myristoyl glycinate, sodium lauroyl glycinate, sodium stearate, oleic acid, sodium palmitate, sodium myristate, lauric acid and sodium/potassium salts thereof, lecithin, soybean lecithin, hydrogenated lecithin.
7. The supramolecular bisabolol eutectic solvent microcapsule according to claim 5, wherein the proportion by weight of the supramolecular bisabolol eutectic solvent, the emulsifier and the solution is that of the supramolecular bisabolol eutectic solvent: emulsifying agent: solution= (0.5-20): (0.5-20): (44-99).
8. A method of preparing the supramolecular bisabolol eutectic solvent microcapsule according to any one of claims 5 to 7, comprising the steps of:
(1) Mixing the supermolecule bisabolol eutectic solvent, the emulsifying agent and the solution, and homogenizing and shearing to obtain a primary emulsion;
(2) And (3) carrying out high-pressure homogenizing shearing on the primary emulsion obtained in the step (1) to obtain the supermolecule bisabolol eutectic solvent microcapsule.
9. The method for preparing the supramolecular bisabolol eutectic solvent microcapsule according to claim 8, wherein the high-pressure homogenizing shearing condition in the step (2) is a temperature of 20-100 ℃ and a pressure of 0-2000bar.
10. Use of the supramolecular bisabolol eutectic solvent micro-lipid vesicles according to any one of claims 5 to 7 in the preparation of cosmetics, health products, food.
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| CN118005529A (en) * | 2024-04-09 | 2024-05-10 | 深圳杉海创新技术有限公司 | Supermolecule panthenol bisabolol and preparation method and application thereof |
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| CN113413325A (en) * | 2021-05-31 | 2021-09-21 | 宝萃生物科技有限公司 | Lip plumping composition and preparation method and application thereof |
| CN115737532A (en) * | 2022-11-29 | 2023-03-07 | 华中科技大学 | Supermolecule salicylic acid composite microneedle patch, and preparation method and application thereof |
| CN115969737A (en) * | 2022-12-08 | 2023-04-18 | 深圳市萱嘉生物科技有限公司 | Supermolecular liposome freeze-dried mask and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113413325A (en) * | 2021-05-31 | 2021-09-21 | 宝萃生物科技有限公司 | Lip plumping composition and preparation method and application thereof |
| CN115737532A (en) * | 2022-11-29 | 2023-03-07 | 华中科技大学 | Supermolecule salicylic acid composite microneedle patch, and preparation method and application thereof |
| CN115969737A (en) * | 2022-12-08 | 2023-04-18 | 深圳市萱嘉生物科技有限公司 | Supermolecular liposome freeze-dried mask and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN118005529A (en) * | 2024-04-09 | 2024-05-10 | 深圳杉海创新技术有限公司 | Supermolecule panthenol bisabolol and preparation method and application thereof |
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